


New Year, New Fling

by CeliPuff



Category: Supernatural
Genre: Castiel is Not Innocent (Supernatural), Castiel/Dean Winchester - Freeform, Castiel/Dean Winchester One Shot, Costume Parties & Masquerades, Dom Castiel/Sub Dean Winchester, M/M, New Year's Eve, One Night Stands, Openly Gay Castiel (Supernatural), Openly Gay Dean Winchester, Team Dean Winchester's Red Ass, Team Dean’s Red Ass, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-01-01
Updated: 2020-01-01
Packaged: 2021-02-27 06:09:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,858
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22082365
Author URL: https://archiveofourown.org/users/CeliPuff/pseuds/CeliPuff
Summary: The Novak’s annual Masquerade ball is a huge hit in their small community. Castiel hates it. His mother is constantly trying to set him up with women even though he’s made it very clear he is gay. The ball may be crawling with willing men and the hookups are hot and promising, but nothing ever makes it past midnight. Cas is sure this year will be no different. Even if this year’s conquest has the most gorgeous green eyes.As for Dean, he’s just looking to get laid.
Relationships: Castiel/Dean Winchester
Comments: 16
Kudos: 242
Collections: Destiel Smash Fest, Team Dean's Red Ass





	New Year, New Fling

**Author's Note:**

> Happy New Years everyone!!

“You’re _gay!_ You should be excited for this Dean!” Charlie stands before him with her hands on her hips, Dean won’t weasel himself out of this one.

“I like to see my man’s face before we fuck Charles. A damn cheesy Masquerade ball is not how I planned on spending my New Years.” Dean eyes the black mask Charlie picked out for him. “You should have gotten me a devil's mask or something, that would have been cool at least.”

“It’s meant to help you find someone for what’s on the inside, not the outside! You lost the bet and then _refused_ to pick out a mask so suck it up, put on the damn mask and can it.”

Charlie is wearing a beautiful jade dress that goes well with her fair skin and bright red hair. Dean thinks it’s a little short but it shows her cute curvy figure well, “I hope there isn’t one lesbian there.” Dean points at her, “karma!”

Charlie rolled her eyes, “I think karma has bigger issues than this Dean.”

“Karma!!” Is all he yells before putting on the stupid mask. He’s wearing a damn penguin suit complete with a bow tie for christ sake, Charlie can quit her bitching.

Dean’s been single for a few months now and he’s _loving_ it. Being single is liberating after a bad breakup and Michael was a controlling asshole that definitely didn’t deserve Dean. He vowed to never give his heart to someone unwilling again, which meant probably never and if you asked him, that was perfectly fine.

**********

Castiel stared at himself in the mirror, he went with black everything this year, hoping to blend. He even chose the most simple black mask he could find.

Last year he went with a blue mask and though he isn’t complaining about the blowjobs, his eyes were like peacock feathers. He’s hoping the black will tone them down.

“Black? Jesus Cassie, it looks like you’re going to a funeral.” Cas is even wearing all black vans, just to piss his parents off. Whatever, he’s here, _again._ Gabriel is wearing all white, of course.

“And you look like Jesus. Must you always be so blinding? Could have at least cut your hair if you weren’t going for that messiah vibe.” Gabriel held out his arms and started humming some gospel and that definitely didn’t help his case, Cas almost choked on his pregame drink laughing.

Cas combed his hair in that, _I just fucked in the bathroom_ , way that he does. A lot of people think Cas just doesn’t comb his hair but Gabriel knows the truth, it’s his _thing._

Everyone has their thing, Gabriel believes he’s the smart one and Cas is the pretty one and he’s okay with that, he’s never had a shortage of ass, people love brains.

It also helps that Gabriel is bi with no standards, “ _What if baskin robbins stopped at one flavor?_ ” Is like his catch phrase but Cas doesn’t care, he’s gay and no one could ever convince him otherwise.

Not that Meg didn’t try a few years back. Cas gave her a shot and that chick didn’t know her way around a dick if it slapped her in the face.

Since before Cas could remember he’s spent every New Years eve here, surrounded by old rich people and their silver spooned offspring.

All he wants is _one year_. One year to do whatever and whoever the _fuck_ he wanted on New Years.

Get drunk downtown at a bar and eat greasy bar burgers, meet a beautiful boy, maybe fall in love. Oh you know, the chick fic shit.

That would _never_ happen here.

Cas invited his friend Charlie from college this year so hopefully they could have some fun tonight. You know, that _mistakes were made_ kinda fun that gays always find together.

These balls have their share of gays and even better, those _in the closet_ gays that feel bold behind a mask. Since Cas was sixteen he’s at the very least, gotten a blowjob every New Years.

It’s so expected it isn’t even fun anymore. Well, that’s a lie, blowjobs are always fun. It’s also fun to bend over some _straight_ guy in his father's office just to show him what he’s missing when he goes home to his boring missionary wife. So, technically Cas can’t say it isn’t fun anymore. But he’d _really_ like something new this year.

He’s twenty five now, isn’t it time for a relationship that lasts longer than a few months? He seems to think so.

Gabriel on the other hand is thirty and thirsty. He isn’t looking to be tied down.

“Let’s go downstairs, people are already showing up.” Gabriel waits in the doorway impatiently.

“Fuck.” Cas mutters to himself and then slides on his mask.

*********

Dean ditches Charlie the moment they enter the Novak estate, instantly making his way to the bar.

The ball exactly what Dean expected. High ceilings, lanterns somehow impossibly hanging all over the grant room. _How the hell do rich people hang these fancy lights?_

“Whiskey, double. Oh and beer.” _Open bar, why the hell not_.

“Double? Let me guess, you were forced here against your will too?” Dean looks over, surprised to see a man leaning against the bar in all black.

“You too huh?” Dean takes a moment to check him out. Dean can tell he’s attractive, he can only see the bottom of his face but it’s a damned good bottom of a face. His five o clock shadow and plump lips have Dean intrigued. “That suit looks like Loki’s in Ragnarok.” _Shit, did I really just make a pop culture reference at a masquerade ball? May as well have an ‘imposter’ sign on my chest._

To his surprise, the man laughs, finally looking over to meet Dean’s gaze. _Are those contacts?_ Dean wonders, _There is no way that blue actually exists._

Dean isn’t the only one thrown off by beautiful eyes though, Cas is completely lost in the most beautiful shade of green he’s ever seen.

“Castiel.” Cas manages to get out, holding out his hand. “And I prefer the other brother personally. Especially after the haircut.”

Dean smiles widely, “Name’s Dean. Not a fan of long hair huh Cas?”

Cas turns to face Dean better, sipping his drink. “No.” Cas checks out Dean’s haircut and it’s just the length he loves. “I like my grip to be right at the base, long hair gets in the way.”

Dean appreciates this man’s candor and holds out his drink to cheers.

“This house is ridiculous right?” Dean asks. “I mean who needs a house this damn big? Talk about over privileged.” Dean jokes and Cas bites back a smile.

“I agree. Not to mention this party is supposed to be against _vanity_ and yet it takes place in this mansion, decked out in decorations that will be tossed in the garbage tomorrow, along with the thousands of dollars worth of food that no one eats. Do you know how much a party like this costs? Almost ten thousand dollars every single year on a single night.” Cas shoots the rest of his drink.

 _Dude must really not want to be here_. “I had no clue it cost that damn much. What a waste, I almost feel bad for the people, don’t you? I mean they spend this much and probably still feel so empty.”

Cas stared at Dean a moment. Truth is, no, he doesn’t feel bad for them because then he’d have to feel bad for himself. “They do.” Is all he says.

Before the conversation can go on, Charlie interrupts, “Dean what the hell, you disappeared the second we walked in. Cas? Hey you found Cas. Your parents house is crazy beautiful dude.”

Cas steals a glance at Dean and laughs at his slack jaw. “Your… shit.” Dean is speechless.

“For the record, you didn’t ask why I was here.” Cas says in his defense.

“Yeah but you just let me shit on your whole family. I’m sorry, really.” _Way to go Winchester._

“Well my family is full of shit so it's all good.” Dean stares at Cas for a moment while Charlie says something about hot chicks and it’s obvious Cas would rather be _anywhere_ else. Dean thinks about how Cas just agreed that the people throwing this party feel empty inside and decides to make it his goal to show this man a good time tonight. _Fuck this party_.

“Cas if you could be doing anything tonight, what would it be?” Dean dives right in, surprising Cas for a moment.

Charlie looks between them both and smiles, “You guys have fun, I’ll see you later.” She knows she probably won’t see them later and that’s okay, they both deserve it.

Cas watches her leave and turns to give Dean his full attention. “Literally anything else.” He admits. “I’ve been stuck here, every single New Years, my entire life. Always the same.”

“Fuck that. New Years is supposed to be exciting and promising. Let’s get out of here.” Dean’s mind is already reeling with ideas to show Cas a good time.

“I do live here, if you want to fuck we could just pick a room.” Cas’ face is hard to read, it’s probably the mask, but Dean can’t tell if a quick fuck is what Cas wants or if he’s just saying what he thinks Dean means.

“That sounds fun but I wasn’t talking about fucking… _yet_.” Dean can see the gleam in Cas’ eyes, they are _definitely_ fucking tonight, but first, Dean is going to show Cas a proper New Years.

Dean holds out his hand, hoping Cas will take it and when he does, both men smile.

Once they’re outside Dean instantly pulls off his mask, “Shit’s uncomfortable right?” He asks, not realizing how taken Cas is with his beautiful face. “These valet drivers better have taken care of my baby.” Dean hands them his ticket and pulls out his phone to tell Charlie to call when she’s ready to go home but she responds quickly with a, _Don’t worry about me, have fun with Cas_. Dean smiles, she really is a great friend.

 _Hope he isn’t disappointed_ , Cas thinks before taking off his own mask and tossing it on the floor. Dean looks up and smiles, “Damn you’re gorgeous.”

Cas runs a hand through his hair, “I think you’re the gorgeous one here.”

Before Dean can respond, he hears the familiar rumble of his beautiful Chevy Impala.

“Alright, this is Baby. She’ll take us anywhere we want to go. Baby, meet Cas.” The proud look on Dean’s face makes Cas smile.

“She’s beautiful.” Cas climbs in and looks over at Dean as he starts the engine. “So, where would you normally be on New Years Eve Dean?”

Dean smiles, “I know just the place.”

The Roadhouse is honestly _exactly_ what Cas pictured and the food is better than any of that expensive bullshit at the ball. Cas’ phone has rang a few times but he turned it off, he’ll deal with his family tomorrow. Tonight, he’s _all_ Dean’s.

People are singing karaoke which would be fun on a normal day but tonight, Dean and Cas sit in a booth and talk the night away.

Obviously they live very different lives but their chemistry is palpable. They enjoy a lot of the same things which matters much more than their upbringing. Dean had a rough start in life but it’s impossible to know that when you meet him. His happy go lucky, give em hell attitude makes Cas admire him.

Cas on the other hand feels unworthy of a man like Dean. He’s had everything handed to him in life and yet all he’s done is complain about how the rich never help the needy. Did he forget he was also rich? Did he forget they he could be helping people too? He’s ashamed when he looks around the bar and sees how happy people are.

Most of their clothes are run down, more than a few are obviously spending their _last_ bit of money here tonight just to ring in the New Year on a positive note.

Cas glances over at Dean and instantly knew what he wanted to do for this rundown bar. “You said you know the owner?” He asks nonchalantly.

“Yeah, she’s like an aunt to me. Her and Bobby raised Sam and I when my dad was on a bender. Which was basically every week.” Dean takes a drink of his beer, “Why?”

Cas shrugs, “Just curious, the food is good so I’ll definitely be returning.” He smiles, hoping that was enough explanation for Dean, it was.

“This food is amazing! I used to work here actually, when I was going to school.” Dean smiles at the memory.

“I can picture you in a little apron.” Cas teases, taking another drink.

Dean laughs, “You would like that huh? Got a little food kink we should discuss Cas?” He teases back.

Cas leaned in closer, his voice is low and deep, “I don’t think you’re ready for my kink list Dean.”

Dean Winchester will _not_ be intimidated, he leans in, closing the gap to a mere inch. “We can sit here all night comparing kinks or we can get out of here and show each other some. Your call, _Castiel_.”

They don’t even make it to the car before Cas has Dean pushed against the side of the building, his tongue invading Dean’s mouth.

Luckily, Dean loves being manhandled and Cas is fucking good at it. His entire being has switched to dominate as his mouth navigates it’s way down Dean’s body, moving Dean’s clothes around as if they personally offend him.

Dean looks around and they are not hidden well at all, anyone could walk on the other side of the road and probably see everything they are doing. “Cas… ah!” Dean is about to suggest they move when Cas bites his hip.

“Shh.” Cas demands turning Dean into putty.

Cas sucks a small mark on Dean’s hip before standing and looking Dean in the eyes. “I just wanted a taste.” Cas smiles at Dean’s glossy blissed out state. “You’re very responsive aren’t you?” Cas steps in closer, his hands gripping Dean’s hips possessively.

All Dean can do is bite his lip, words completely failing him.

Cas takes a step back, allowing them a second to breathe. Cas pulls Dean by his hand and they finally make their way to Baby.

When the engine purrs, Dean notices the time. _11:27_ , Good thing Dean lives less than ten minutes away. That’s just enough time to get back to his appartment and fuck into the New Year. _Hell yeah._

Dean flips on the tv and puts the volume up, he wants to hear the countdown but has no intention of watching it.

Cas makes himself comfortable, removing his jacket, tie and shoes near the door. Both are pleased to see the others erections still going strong as Cas unbuttons Dean’s shirt.

Dean can see Cas loves his body by the way he licks his lips, which isn’t surprising, Dean’s always had an amazing body. Dean reaches to unbutton Cas’ shirt, and soon their smooth bare chests are together just like their tongues.

Cas sucks down Dean’s neck and bites again, Dean takes a mental note that Cas, is a biter and realizes he actually _loves_ it.

Dean is so strung on Castiel he doesn’t even notice Cas was working his pants that whole time until he feels a breeze against his dick as it bobs free. When Cas wraps his large hands around it they both groan happily.

“So hard for me already?” Cas asks breathlessly as he kisses down Dean’s chest and stomach.

“All for you Cas.” Dean manages to grit out, finally forming a sentence. Cas is pleased again, Dean feels his smile against his skin.

That first lick has Dean’s head falling back in pleasure and reaching down to grip Cas’ thick onyx locks. The moan that escapes Cas has Dean taking another mental note and pulling harder. Cas swallows Dean down, groaning and bobbing as Dean fucks into his mouth.

Dean looks down to discover Cas is enjoying this just as much as Dean is. _How is Cas on his knees before me and still so fucking dominate?_ Cas has a cock between his lips and he’s still telling Dean exactly what to do with those stormy ocean eyes.

Dean had to pull Cas off by his hair, he knew it would just turn him on more but unless Cas wanted this fun to end prematurely he’d have to get that angelic mouth off of Dean’s throbbing cock.

“Come on angel, you know I want that cock.” Dean’s panting, willing away his orgasm by gripping the base of his dick.

Cas stood with a grin, “I didn’t hear you say please.” Cas challenges as he unbuckles his slacks.

 _Fuck_. “Please.” Dean grunts, “Please fuck me so I feel you in my sleep.”

The look Cas gives Dean has him squirming. “You’re mouthy.” He grips Dean’s chin and it doesn’t matter that Dean has at least an inch on the man, Cas is the one in control. “Show me.” He orders.

Dean grins, “Yes Castiel” and drops to his knees. Dean’s a cocky little bastard with blowjobs and he’s determined to show Cas he isn’t the only one with a magic tongue. Within minutes, Cas is the one panting and pulling Dean off of him.

Cas smiles, he can tell Dean is very proud of himself. “Yes very mouthy, I love it. Turn around.” Dean realizes then they never made it past the living room.

“Uh… bedroom?” He offers. Dean can tell Cas almost considers staying put but then nods for Dean to lead the way.

Dean pulls out his box of condoms and a bottle of lube, handing it to Cas. “Don’t be a gentleman.” Dean winks, he’s always been a power bottom. Not a lot of tops can handle such a powerful bottom but Cas doesn’t seem to mind.

His eyes are like blue flames when he turns Dean and reaches around, gripping his cock from behind with his own cock between Dean’s cheeks. Cas pulls Dean’s hair so he can kiss and mouth at his cheek and jaw while he strokes him. “Fuck Cas, come on.” Cas releases Dean and steps back.

_Smack._

Cas looks down at Dean’s beautiful red ass and rubs it. “You will take what I give you Dean.”

Dean does everything to hide the enjoyment from his voice, “Yes Castiel” he whispers, wondering how he could get Cas to spank him again. _Just one more before we fuck._

After Cas applies lube to his fingers, he plays with Dean’s ass a while more, making Dean writhe beneath him. The second Cas’ finger enters, Dean pushes back and smiles to himself, awaiting his spanking.

Cas bit his bottom lip, trying not to smile. “So needy.”

 _Smack_.

Dean tossed his head back, groaning in pleasure, he needs Cas to fuck him like yesterday.

Luckily, Cas needs it too.

He rolls a condom on and pushes inside with ease, bottoming out in seconds. Cas sits there for a few moments, letting Dean adjust before he starts moving.

With all the teasing and pining tonight, neither of them are going to last long. Cas is a generous lover, never neglecting Dean’s cock as he pounds into him relentlessly. Yeah, Dean is _definitely_ going to feel him for a few days.

Cas makes sure Dean comes first, as soon as he finds that perfect angle that has Dean pushing back into him with his head rolling back, Cas strokes Dean to completion, praising him, kissing and sucking on his shoulder until he sighs happily.

But Cas isn’t done with Dean’s ass yet, he pushes Dean down onto the bed, his back arched perfectly while he grips Dean’s hips like he might fly away, drilling his ass until he comes.

And that was just round one.

<<<<<<<<<<>>>>>>>>>>

Dean’s the first to wake up and he’s reminded of the night before when he shifts in his bed, “Ah!” _Fuck my ass is sore!_

Cas grunts next to him, it sounds like he’s trying to communicate in some sleepy bratty way so Dean leans in, “You say something Cas?”

He grunts again, this time it sounded like he said “No” but he’s refusing to move an inch.

“Wake up angel.” Dean starts kissing Cas’ shoulder, laughing when Cas grunts _no_ again.

Dean sighs, knowing exactly what Cas needs. _Coffee_. Dean gets out of bed and makes his way to the kitchen.

Cas is still sleeping when Dean returns. He sets a hot cup of coffee next to Cas’ side and climbs back in bed with his own, smiling down at the innocent looking man who just wrecked his ass last night, multiple times.

Dean can tell the moment Cas smells the coffee, his eyes flutter open and he frowns at Dean.

“What? You have a cup too.” Dean nods towards the nightstand and laughs at how adorable Cas looks when he’s grumpy.

“I don’t want to be awake yet. Why are we awake?” Cas rolls onto his back with a groan. “Please tell me you’re not a morning person.”

Dean laughs, “Aren’t you just a ray of sunshine? Sit up and drink, I have work in a couple hours.”

Sighing, Cas sits up. “Are you kicking me out?” He grabs his coffee and takes a long dramatic sip.

“Yes, I am actually but only because I agreed to open the shop for a couple hours. People need their cars fixed on New Years, I actually should have opened an hour ago but,” Dean shrugs, “kinda had a crazy night.”

“Yeah it was a night to remember.” Cas takes another drink and gets out of bed. “Thanks for a great night. I really needed that.” Cas starts getting dressed.

“I know I said I was kicking you out, but I didn’t mean right now. We have time to coffee and maybe even grab breakfast, depending on how fast you can make me come once you finish your coffee.” Dean take another sip innocently.

Cas shakes his head but grabs his phone and climbs back into bed. Cas turns the phone on and picks up his mug to drink while he reads his text messages, “My parents are pissed.” Cas laughs and sets the phone down on the comforter.

Dean takes the opportunity to pick it up and put his phone number in it. “You know, for round two.” He winks.

Cas rolls his eyes, “Round two was last night. So was three, and four is in about ten minutes. Sure you haven’t had enough?”

“Yeah Cas, I’m positive.” Dean suddenly can’t remember why he wants to be single.

“Yeah, I haven’t either.” Cas admits happily. He already planned on anonymously donating a shit ton of money towards the Roadhouse, he may as well see where things go with this beautiful green eyed man.


End file.
